Peter makes Debra Whitman cry, drink!

You'd be hard-pressed to find an issue he didn't make her cry, though. From 1982, Peter Parker, the Spectacular Spider-Man #67, "Boomerang, the Killer Who Keeps Coming Back!" Written by Bill Mantlo, pencils by Edward Hannigan, inks by Allen Milgrom.

The cover promises "Adventure! Mystery! Romance! Face it, friend, this issue has it all!" But it might be a bit short on the romance front, as Peter's study buddy/potential love interest Marcy Kane is so cheesed at him for breaking a study session to fight Electro that she drops his books off at the school's lost-and-found; and Peter continues to treat Debra Whitman as a doormat. This was during a particularly sad-sack stretch for Peter, as he was also doing terribly in grad school and facing more competition in his photography job for the Bugle, in the person of Lance Bannon. Also competing for a job this month: Boomerang, angling for the staff assassin job with the Kingpin! It's weird, but that was treated like a position or a cabinet post at the time. Boomerang murders a snitch that turned state's evidence, figuring that would put him in good with the Kingpin, and it really doesn't: Kingpin claims to have been feeding the snitch false evidence for years, in order to lead the feds away from his real activities.

The Kingpin gives Boomerang a second chance: kill Spider-Man, and there might be a job for him. It's mostly just to get rid of him, but I suppose there's always the chance he'll get lucky. He doesn't though. In a running fight that goes through the Daily Bugle, Spidey beats Boomerang, and manages to throw Bannon's camera out the window to boot. (He thinks he'll pay for a new one; like he's ever got that kind of cash.)

Boomerang has largely been played for laughs since Superior Foes of Spider-Man or earlier, but he legit murdered a guy here. Not for the last time either, I don't think.